EP0017209B1 - Sels d'alcoylammonium substitués, leur préparation et leur utilisation pour la régulation de la croissance des plantes - Google Patents

Sels d'alcoylammonium substitués, leur préparation et leur utilisation pour la régulation de la croissance des plantes Download PDF

Info

Publication number
EP0017209B1
EP0017209B1 EP80101709A EP80101709A EP0017209B1 EP 0017209 B1 EP0017209 B1 EP 0017209B1 EP 80101709 A EP80101709 A EP 80101709A EP 80101709 A EP80101709 A EP 80101709A EP 0017209 B1 EP0017209 B1 EP 0017209B1
Authority
EP
European Patent Office
Prior art keywords
denotes
formula
substituted
cyano
alkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
EP80101709A
Other languages
German (de)
English (en)
Other versions
EP0017209A1 (fr
Inventor
Hubert Dr. Sauter
Bernd Dr. Zeeh
Ernst Dr. Buschmann
Johann Dr. Dipl.-Landw. Jung
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to AT80101709T priority Critical patent/ATE2080T1/de
Publication of EP0017209A1 publication Critical patent/EP0017209A1/fr
Application granted granted Critical
Publication of EP0017209B1 publication Critical patent/EP0017209B1/fr
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/46—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom rings with more than six members
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/40—Oxygen atoms
    • C07D211/42—Oxygen atoms attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
    • C07D295/104—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/108—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/15—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
    • C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T70/00—Locks
    • Y10T70/50—Special application
    • Y10T70/5093—For closures
    • Y10T70/5146—Window
    • Y10T70/515—Sliding sash
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T70/00—Locks
    • Y10T70/50—Special application
    • Y10T70/5093—For closures
    • Y10T70/5155—Door
    • Y10T70/5159—Emergency exit
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T70/00—Locks
    • Y10T70/50—Special application
    • Y10T70/5093—For closures
    • Y10T70/5155—Door
    • Y10T70/5168—Braces
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T70/00—Locks
    • Y10T70/50—Special application
    • Y10T70/5093—For closures
    • Y10T70/5155—Door
    • Y10T70/5173—Sliding door

Definitions

  • the invention relates to new substituted alkylammonium salts, namely certain aryloxy and arylthioalkylammonium salts, agents for regulating plant growth which contain these compounds, the use of these compounds and agents for regulating plant growth, and processes for the preparation of the new compounds.
  • quaternary ammonium compounds of completely different structure than plant growth regulators are described, e.g. B. 2-chloroethyl-trimethylammonium chloride (CCC, U.S. Patent 3,156,544).
  • CCC 2-chloroethyl-trimethylammonium chloride
  • U.S. Patent 3,156,544 2-chloroethyl-trimethylammonium chloride
  • these compounds are not quaternary aryloxyalkylammonium salts or arylthioalkylammonium salts; their effect is also not always satisfactory, especially when the application rates are low.
  • the invention relates to substituted alkylammonium salts of the formula 1 in the
  • Ar means, for example, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 2,4-dichlorophenyl, '3,4-dichlorophenyl, 3,5-dichlorophenyl, 2,6-dichlorophenyl, 2,4,5-trichlorophenyl, 2,4,6- Trichlorophenyl, '2-chloro-4-fluorophenyl, 2-chloro-4-bromophenyl, 2-methyl-4-chlorophenyl, 2-chloro-4-phenylphenyl, 2-benzyl-4-chlorophenyl, 3,' 5- Diethylphenyl, 2,4,6-trimethylphenyl, '2,6-dichloro-4-nitrophenyl, 2,6-diiodo-4-cyanophenyl, 2-methoxy-4-methylphenyl, 4-cyanophenyl, 3-nitrophenyl, 2- -Methyl-4-methylthiophenyl, 4-
  • B stands for the pyrrolizidine bicyclic ring or for a pyrrolidine, piperidine, piperidine, morpholine or hexamethyleneimine ring substituted on the quaternary N by R 3 .
  • R 3 radicals are methyl, ethyl, propyl, butyl, allyl, propargyl, 2-chloroethyl, 2-bromoethyl, cyanomethyl, methylcarbonylmethyl, 2-chloropropen-3-yl, 2-methylpropen-3-yl and 2-buten-1 -yl.
  • the anion Z6 can be chosen as desired from the non-phytotoxic acids.
  • Ze means, for example, acetate, methyl sulfonate, p-toluenesulfonate, p-dodecylbenzenesulfonate, nitrate, phosphate, iodide, sulfate, methosulfate and in particular chloride or bromide.
  • the anion Ze is normally determined by the choice of the quaternizing agent of the formula 11 or V; however, other anions Ze can then be easily introduced by ion exchange using generally known methods (see, for example, Houben-Weyl, Methods of Organic Chemistry, Volume 11/2, pp. 620-626 and Volume 1/1, p. 544, Thieme Verlag, Stuttgart 1958).
  • Chlorine, bromine, iodine, methyl sulfonate or p-toluenesulfonate are particularly suitable as the nucleofugic leaving group for process a).
  • the reaction of the compounds II and III can in the presence or absence of a solvent or diluent, such as water or the usual organic solvents, for.
  • a solvent or diluent such as water or the usual organic solvents, for.
  • the reactants II and III can be used in any quantitative ratios, preference is given to equimolecular amounts or an excess of amine III.
  • the compounds of formula II are generally known compounds or can be easily prepared by known methods, e.g. B. by monoalkylation of phenols ArOH or thiophenols ArSH with aliphatic dihalides, such as 1,2-dibromoethane, 1,3-dibromopropane or 1,4-dibromobutane, preferably in water or particularly preferably in boiling diethyl ketone or cyclopentanone in the presence of at least equivalent amounts Potassium carbonate, (see Houben-Weyl, Methods of Organic Chemistry, Volume 6/3, pp. '54 -59, Thieme-Verlag, Stuttgart 1965 as well as Examples 1 and 3).
  • aliphatic dihalides such as 1,2-dibromoethane, 1,3-dibromopropane or 1,4-dibromobutane, preferably in water or particularly preferably in boiling diethyl ketone or cyclopentanone in the presence of at least equivalent amounts Potassi
  • tertiary amines of the formula III which can be used are N-methylpyrrolidine, N-ethylpyrrolidine, N-allylpyrrolidine, N-propylpyrrolidine, N-butylpyrrolidine, N-methylpiperidine, N-methylhexamethyleneimine, 2,4,6-trimethylmorpholine, quinuclidine or pyrrolizidine.
  • alkyl chloride of the formula V can be used, for example, methyl chloride, methyl bromide, methyl iodide, dimethyl sulfate, allyl bromide, propargyl chloride, isopentyl bromide, chloroacetone, chloroacetonitrile or 2-methoxyethyl tosylate.
  • the alkylation is carried out without diluent or solvent or in the presence of a diluent or solvent, such as water, ethanol, acetone, acetonitrile, ethyl acetate, ether, toluene or dimethylformamide, in a homogeneous or inhomogeneous phase at temperatures between 0 and 150 ° C, preferably 20 and '120 ° C.
  • a diluent or solvent such as water, ethanol, acetone, acetonitrile, ethyl acetate, ether, toluene or dimethylformamide
  • the tertiary amines of formula IV are known compounds or easily accessible by known methods, e.g. B. according to the scheme by alkylation of secondary amines of the formula VI, in which Y has the meaning given above, with the compounds of the formula II mentioned above.
  • the reaction conditions here correspond to those of the reaction according to Scheme II + III - I, with a 2- to 10-fold molar excess of the amine of formula VI is preferred.
  • the HX formed during the reaction can easily e.g. B. by treating the product mixture with aqueous alkali hydroxides or by filtering off an optionally added acid addition salt. HZ can be removed (see example 2).
  • tertiary amines of the formula IV Another method known per se for the synthesis of tertiary amines of the formula IV consists in the reaction of phenols or thiophenols of the formula VII or their alkali metal salts, in which Ar and X have the meaning given above, with tertiary amines of the formula VIII or their acid addition salts where R 1 , n, R 2 and Y have the meanings given above and in which Z represents a nucleofugic leaving group, preferably chlorine, bromine, iodine, methanesulfonate or p-toluenesulfonate (see Houben-Weyl, Methods of Organic Chemistry, Volume 6 / 3, pp. 54-59, Thie me Verlag, Stuttgart 1965) and Example 4 according to the scheme:
  • Examples of amines of the formula VIII which can be used are N- (2-chloroethyl) pyrrolidine, N- (2-chloroethyl) piperidine, N- (2-chloropropyl) pyrrolidine or N- (2-chloroethyl) hexamethyleneimine.
  • a solution of 85 g of N- (2-chloroethyl) pyrrolidinium hydrochloride is added dropwise to the mixture of 100 g of sodium hydroxide and 160 g of 2,4,5-trichlorothiophenol in 2400 ml of water under nitrogen and with stirring and the mixture is then boiled under reflux for 8 hours . After cooling, the precipitate is filtered off, taken up in 1000 ml of methylene chloride and washed twice with 200 ml of 10% aqueous sodium hydroxide solution and once with 200 ml of water.
  • the new active substances according to the invention intervene in the metabolism of the plants and can therefore be used as growth regulators.
  • growth regulators should positively influence the crop plants in the desired manner.
  • the vegetative growth of the plants can be strongly inhibited, which manifests itself in particular in a reduction in the growth in length.
  • the use of the compounds according to the invention leads to an increased chlorophyll content and thus to a darker leaf color. As a result, an increased photosynthesis rate and thus an increased yield formation can be expected.
  • z. B the reduction of grass cover on road edges, canal embankments and on lawns such as parks, sports and east facilities, decorative lawns and airfields, so that the labor-intensive and costly lawn cutting can be reduced.
  • growth regulators can also increase or inhibit the lateral branching of the plants. There is interest if, for. B. in tobacco plants the formation of side shoots (stinging shoots) should be inhibited in favor of leaf growth.
  • Another mechanism of increasing earnings with growth inhibitors is based on that the nutrients benefit flower and fruit formation to a greater extent, while vegetative growth is restricted. Furthermore, because of the relatively small mass of leaves or plants, the infestation with various, in particular fungal, diseases can be prevented.
  • the inhibition of vegetative growth also enables denser planting in many crops, so that an additional yield can be achieved based on the soil area.
  • the compounds according to the invention are particularly suitable for inhibiting vegetative growth in crop plants such as soybeans, sunflowers, peanuts, oilseed rape, ornamental plants, cotton, rice and grasses.
  • the new substances can increase yields by interfering with plant metabolism or by promoting or inhibiting vegetative and / or generative growth.
  • plant growth regulators can both shorten or lengthen the growth stages and accelerate or delay the ripeness of the harvested parts of the plant before or after the harvest.
  • Ease of harvest for example, is of economic interest, which is made possible by the time-related falling or decreasing of the adhesive strength on the tree in the case of citrus fruits, olives or other types and varieties of pome, stone and nuts.
  • the same mechanism that is, the promotion of the formation of separating tissue between the fruit or leaf and shoot part of the plant is also essential for a well controllable defoliation of the trees.
  • the effect of the new compounds is better than that of known growth regulators.
  • the effect is evident both with monocots, e.g. B. cereals such as wheat, barley, rye, oats and rice or corn or grasses and in particular in the case of dicotyledons (e.g. sunflowers, tomatoes, peanuts, vines, cotton, rapeseed and especially soybeans) and various ornamental plants such as chrysanthemums, poinsettias and hibiscus.
  • monocots e.g. B. cereals such as wheat, barley, rye, oats and rice or corn or grasses
  • dicotyledons e.g. sunflowers, tomatoes, peanuts, vines, cotton, rapeseed and especially soybeans
  • various ornamental plants such as chrysanthemums, poinsettias and hibiscus.
  • the active compounds according to the invention can be added to the crop plants both from the seed (as a seed dressing) and via the soil, ie. H. through the root and - particularly preferably - by spraying over the leaf.
  • amounts of active ingredient of 0.001 to 50 g per kilogram of seed, preferably 0.01 to 10 g, are generally required.
  • the agents according to the invention can be used in the form of customary formulations, such as solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the application forms depend entirely on the purposes; in any case, they should ensure a fine and uniform distribution of the active substance.
  • the formulations are prepared in a known manner, e.g. B. by stretching the active ingredient with solvents and / or carriers, optionally using emulsifiers and dispersants, and in the case of the use of water as a diluent, other organic solvents can also be added.
  • Solvents such as aromatics (e.g. xylene, benzene), chlorinated aromatics (e.g.
  • chlorobenzenes paraffins (e.g. petroleum fractions), alcohols (e.g. methanol, butanol) are essentially suitable as auxiliaries for the formulation ), Amines (e.g. ethanolamine), ketones (e.g. cyclohexanone), dimethylformamide and water; solid carriers such as natural powdered rock (e.g. kaolins, clays, talc, chalk) and synthetic powdered rock (e.g. highly disperse silica, silicates); Emulsifiers or other surface-active agents, such as nonionic and anionic emulsifiers (e.g.
  • the compounds according to the invention are preferably used in aqueous solution, if appropriate with the addition of water-miscible organic solvents such as methanol or other lower alcohols, acetone, dimethylformamide or N-methylpyrrolidine.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90.
  • formulations or the ready-to-use preparations produced therefrom such as solutions, emulsions, suspensions, powders, dusts, pastes or granules, are used in a known manner, for example in the pre-emergence process, in the post-emergence process or as a mordant.
  • the agents according to the invention can also be present in these application forms together with other active ingredients, such as.
  • B. herbicides, insecticides, growth regulators and fungicides or mixed with fertilizers and applied.
  • growth regulators When mixed with growth regulators, the spectrum of action is enlarged in many cases.
  • a number of such growth regulator blends also have synergistic effects.
  • H. the effectiveness of the combination product is greater than the added effectiveness of the individual components.
  • Polychloronitrobenzenes such as pentachloronitrobenzene, methyl isocyanate, fungicidal antibiotics, such as griseofulvin or kasugamycin, tetrafluorodichloroacetone, 1-phenylthiosemicarbazide, Bordeaux mixture, nickel-containing compounds and sulfur.
  • test plants were grown on peat culture substrate which was adequately supplied with nutrients in plastic vessels of approximately 12.5 cm in diameter.
  • soybeans of the SRF 400 variety were grown on a neutral, loamy sandy soil, which was sufficiently supplied with nutrients, in Mitscherlich vessels under optimal conditions in a climatic chamber.
  • the test substances were applied post-emergence by spraying the plants with aqueous preparations of the substances.
  • the application rates applied corresponded to 0.5, 1.0 and 1.5 kg of active ingredient / ha. Two vessels each formed an experimental variant. At the end of the test, the observed shortening effect was confirmed by measuring the height of the plant. These measured values were related to the height of the untreated plants.
  • the individual data can be found in the table.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Environmental Sciences (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Hydrogenated Pyridines (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Hydroponics (AREA)
  • Plural Heterocyclic Compounds (AREA)

Claims (10)

  1. pour les Etats contractants BE, CH, DE, FR, GB, IT, LU, NL, SE
  2. 1. Sels d'alkylammonium substitués de formule I
    Figure imgb0061
    dans laquelle
    Ar représente prényle, qui est substitué par un groupe trifluorométhyle, nitro, cyano, C2-C4--alkylcarbonyle, C2-C4-alkylcarbonylamino ou par 2 à 3 des substituants suivants, identiques ou différents: alkyle, alcényle, alkinyle, cycloalkyle, alcoxy, alcényloxy, alkinyloxy, alkylthio, halogénalkyle, halogénalcoxy, halogénalkylthio, alkylcarbonylamino, alkylsulfonyle, alkylaminosulfo- nyle, dialkylaminosulfonyle ayant chacun jusqu'à 6 atomes C, fluor, chlore, brome, iode, nitro, cyano, aminosulfonyle, phényle ou benzyle
    X représente oxygène ou soufre
    n est le nombre 0, 1 ou 2
    R' et R2 sont identiques ou différents et représentent hydrogène ou alkyle en C,-C4
    B représente un bi-cycle quinuclidine ou pyr- rolizidine, ou le groupe
    Figure imgb0062
    dans lequel Y est mis pour un groupe -(CH2)4-, -(CH2)5-, -(CH2)6-, -(CH2)7-, -CH2-CH=CH-(CH2)2-, -(CH2)2-O-(CH2)2-, -(CH2)2-S-(CH2)2-, -NH-(CH2)4--NH-CH2-CH=CH-CH2- éventuellement substitué par 1 à 3 restes, identiques ou différents, C1-C4-alkyle, -alcoxy, -halogénalkyle, chlore, brome, hydroxy ou cyano,
    R3 représente alkyle, alcényle ou alcinyle en C,-C, à chaîne droite ou ramifiée, qui peut être substitué par halogène, hydroxy, cyano, alcoxy ou alkylcarbonyle en C1-C4,
    Z représente l'anion d'un acide HX quelconque, non phytotoxique.
  3. 2. Procédé de préparation de sels d'alkylammonium substitués de formule I selon la revendication 1, caractérisé par le fait que
    a) on fait réagir des composés de formule II
    Figure imgb0063
    dans laquelle Ar, X, R1, n et R2 ont les significations sus-indiquées, et Z est mis par un groupe de départ nucléofuge, avec une amine tertiaire de formule III
    Figure imgb0064
    où B a les significations sus-indiquées, ou
    b) on alkyle, à l'état de sel quaternaire de formule I, des composés de formule IV
    Figure imgb0065
    dans laquelle Ar, X, R1, n, R2 et Y ont les significations sus-indiquées, avec des moyens d'alky- lation de formule V
    Figure imgb0066
    dans laquelle R3 a la signification sus-indiquée et Z est mis par un groupe de départ nucléofuge.
  4. 3. Moyen de régularisation de la croissance des plantes, contenant un ou plusieurs composés selon la revendication 1.
  5. 4. Moyen de régularisation de la croissance des plantes contenant un ou plusieurs composés de la revendication 1 et un support solide ou liquide, ainsi qu'éventuellement un ou plusieurs agents tensio-actifs.
  6. 5. Utilisation de composés selon la revendi- 5 cation 1 pour régulariser la croissance des plantes.
  7. 6. Procédé de préparation de moyens régularisant la croissance des plantes, caractérisé par le fait qu'on mélange un ou plusieurs com- 10 posés selon la revendication 1 avec des supports solides ou liquides ainsi qu'éventuellement un ou plusieurs agents tensio-actifs.
EP80101709A 1979-04-04 1980-03-31 Sels d'alcoylammonium substitués, leur préparation et leur utilisation pour la régulation de la croissance des plantes Expired EP0017209B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT80101709T ATE2080T1 (de) 1979-04-04 1980-03-31 Substituierte alkylammoniumsalze, ihre herstellung und verwendung zur regulierung des pflanzenwachstums.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19792913523 DE2913523A1 (de) 1979-04-04 1979-04-04 Substituierte alkylammoniumsalze, ihre herstellung und verwendung zur regulierung des pflanzenwachstums
DE2913523 1979-04-04

Publications (2)

Publication Number Publication Date
EP0017209A1 EP0017209A1 (fr) 1980-10-15
EP0017209B1 true EP0017209B1 (fr) 1982-12-22

Family

ID=6067419

Family Applications (1)

Application Number Title Priority Date Filing Date
EP80101709A Expired EP0017209B1 (fr) 1979-04-04 1980-03-31 Sels d'alcoylammonium substitués, leur préparation et leur utilisation pour la régulation de la croissance des plantes

Country Status (9)

Country Link
US (1) US4350518A (fr)
EP (1) EP0017209B1 (fr)
JP (1) JPS55133358A (fr)
AT (1) ATE2080T1 (fr)
BR (1) BR8001986A (fr)
CA (1) CA1144922A (fr)
DE (2) DE2913523A1 (fr)
HU (1) HU182685B (fr)
SU (1) SU1009268A3 (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3103069A1 (de) * 1981-01-30 1982-08-26 Basf Ag, 6700 Ludwigshafen Dibenzofuranderivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide
DE3230087A1 (de) * 1982-08-13 1984-02-16 Basf Ag, 6700 Ludwigshafen Cyclohexan-1,3-dion-derivate, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung unerwuenschten planzenwuchses
JPS59106460A (ja) * 1982-12-10 1984-06-20 Fujisawa Pharmaceut Co Ltd Ｎ−含有複素環化合物誘導体
AU5940186A (en) * 1985-07-05 1987-01-08 Institut Fur Pflanzenschutzforschung 2, 6 - dimethyl - morpholine quartenary compounds
JPS6225259A (ja) * 1985-07-26 1987-02-03 Mitsubishi Electric Corp 電磁超音波トランスジユ−サ
US5385912A (en) * 1991-03-08 1995-01-31 Rhone-Poulenc Rorer Pharmaceuticals Inc. Multicyclic tertiary amine polyaromatic squalene synthase inhibitors
CN110698389B (zh) * 2019-11-12 2022-10-04 河南省科学院高新技术研究中心 N-[2-(2-甲氧基-5-硝基-苯氧基)乙基]卤化吡啶及其制备方法和应用
AU2021236130A1 (en) * 2020-03-11 2022-09-22 Nocion Therapeutics, Inc. Charged ion channel blockers and methods for use

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3255196A (en) * 1966-06-07 Phenoxyalkyl piperidine derivatives
BE588558A (fr) * 1959-03-13 1960-09-12
GB952736A (en) * 1959-06-16 1964-03-18 Wellcome Found Quaternary ammonium compounds and their preparation
GB982572A (en) * 1960-06-10 1965-02-10 Wellcome Found Improvements in and relating to quaternary ammonium compounds and the preparation thereof
US3142554A (en) * 1961-10-10 1964-07-28 Monsanto Co Controlling vegetation with aryl thioalkylamines
US3275629A (en) * 1963-03-20 1966-09-27 Monsanto Co Substituted aryloxyalkylene amines
CH502760A (de) * 1967-01-04 1971-02-15 Basf Ag Mittel zur Hemmung des Pflanzenwachstums und zur Änderung des Pflanzenhabitus
CH518059A (de) * 1969-04-22 1972-01-31 Ciba Geigy Ag Pflanzenwachstum regulierendes Mittel
US3564046A (en) * 1969-05-16 1971-02-16 Amchem Prod Quaternary ammonium derivatives of limonene
BE764656A (fr) * 1970-03-25 1971-09-22 Fujisawa Pharmaceutical Co Nouveaux sels d'ammonium quaternaire et leur application a la regulation de la croissance des plantes
BE795155A (fr) * 1972-02-10 1973-08-08 Cassella Farbwerke Mainkur Ag Composes d'ammoniums quaternaires utilisables comme adjuvants en teinturerie

Also Published As

Publication number Publication date
SU1009268A3 (ru) 1983-03-30
DE3061398D1 (en) 1983-01-27
US4350518A (en) 1982-09-21
JPS55133358A (en) 1980-10-17
ATE2080T1 (de) 1983-01-15
HU182685B (en) 1984-02-28
BR8001986A (pt) 1980-11-25
EP0017209A1 (fr) 1980-10-15
JPS64947B2 (fr) 1989-01-10
DE2913523A1 (de) 1980-10-23
CA1144922A (fr) 1983-04-19

Similar Documents

Publication Publication Date Title
EP0315850B1 (fr) Procédé pour influencer la croissance des plantes par des azolylméthyloxiranes
EP0040350A1 (fr) Nouveaux composés azoliques, leur préparation, leur utilisation pour le traitement des plantes et compositions à cette fin
EP0078509B1 (fr) Dérivés d'acétylène, leur procédé de préparation et leur utilisation pour la régulation de la croissance des plantes
EP0017209B1 (fr) Sels d'alcoylammonium substitués, leur préparation et leur utilisation pour la régulation de la croissance des plantes
EP0044407B1 (fr) Dioxan-1,3-yl-5-alkyltriazoles, leur préparation et leur emploi comme régulateurs de croissance de plantes
EP0026872B1 (fr) Produits régulateurs de la croissance des plantes contenant des sels d'alkylammoniums substitués et leurs utilisation
EP0043923B1 (fr) Dioxan-1,3-yl-5-alkényltriazoles, leur préparation et leur emploi comme régulateurs de croissance de plantes
EP0095677B1 (fr) Triazolyl-cétonoximes et dioximes, leur procédé de préparation et leur application comme agents régulateurs de croissance des plantes
EP0229642B1 (fr) Dérivés d'azoles, fongicides et régulateur de croissance les contenant
EP0056087B1 (fr) Application d'alpha-azolylglycols comme régulateurs de la croissance des plantes
DD152467A5 (de) Mittel zur regulierung des pflanzenwachstums
EP0363766B1 (fr) Azolylméthylcyclopropanes et leur application comme produits protecteurs pour plantes
DE3215360A1 (de) Bisazolyl-verbindungen, ihre herstellung, ihre verwendung zur regulierung des pflanzenwachstums und mittel dafuer
EP0270002B1 (fr) Dérivés de cyclohexénone
EP0076446A2 (fr) Azolylalkyl-2,3-dihydrobenzofuranes ayant une action de régulateurs de croissance des plantes et leur application
DE2601376A1 (de) Phenoxycarbonsaeure-aryloxy(thio)carbonylaminomethylester, verfahren zu ihrer herstellung sowie ihre verwendung zur regulierung des pflanzenwachstums
DE3604871A1 (de) Cyclohexenonderivate, verfahren zu ihrer herstellung und ihre verwendung als mittel zur regulierung des pflanzenwachstums
DE3523862A1 (de) Mittel zur regulierung des pflanzenwachstums
EP0092100B1 (fr) Triazolylalkyl-2,3-dihydrobenzofuran-oximes, leur procédé de préparation et leur application comme agents régulateurs de croissance des plantes
DE3435944A1 (de) Vinyl-carbamoyl-imidazole enthaltende mittel zur regulierung des pflanzenwachstums
DE3143721A1 (de) Acetylenverbindungen, verfahren zu ihrer herstellung und ihre verwendung zur regulierung des pflanzenwachstums
DE3143722A1 (de) Acetylenverbindungen, verfahren zu ihrer herstellung und ihre verwendung zur regulierung des pflanzenwachstums
DE3321183A1 (de) Triazolyl-ketonoxime und -dioxime, verfahren zu ihrer herstellung und ihre verwendung als pflanzenwachstumsregulatoren
DE3143720A1 (de) Acetylenverbindungen, verfahren zu ihrer herstellung und ihre verwendung zur regulierung des pflanzenwachstums
DE3923151A1 (de) 1,2-dihalogenazolylethanderivate und diese enthaltende pflanzenschutzmittel

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Designated state(s): AT BE CH DE FR GB IT LU NL SE

17P Request for examination filed

Effective date: 19801209

ITF It: translation for a ep patent filed

Owner name: ING. C. GREGORJ S.P.A.

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Designated state(s): AT BE CH DE FR GB IT LU NL SE

REF Corresponds to:

Ref document number: 2080

Country of ref document: AT

Date of ref document: 19830115

Kind code of ref document: T

REF Corresponds to:

Ref document number: 3061398

Country of ref document: DE

Date of ref document: 19830127

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LU

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19830331

ET Fr: translation filed
PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: SE

Payment date: 19890227

Year of fee payment: 10

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SE

Effective date: 19900401

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 19910213

Year of fee payment: 12

Ref country code: AT

Payment date: 19910213

Year of fee payment: 12

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: CH

Payment date: 19910214

Year of fee payment: 12

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: BE

Payment date: 19910301

Year of fee payment: 12

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 19910315

Year of fee payment: 12

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 19910319

Year of fee payment: 12

ITTA It: last paid annual fee
PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: NL

Payment date: 19910331

Year of fee payment: 12

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Effective date: 19920321

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Effective date: 19920331

Ref country code: CH

Effective date: 19920331

Ref country code: BE

Effective date: 19920331

Ref country code: AT

Effective date: 19920331

BERE Be: lapsed

Owner name: BASF A.G.

Effective date: 19920331

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Effective date: 19921001

NLV4 Nl: lapsed or anulled due to non-payment of the annual fee
GBPC Gb: european patent ceased through non-payment of renewal fee
PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Effective date: 19921130

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

EUG Se: european patent has lapsed

Ref document number: 80101709.6

Effective date: 19910110

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT